Synthesis of anisolylated aspartyl and glutamyl tripeptides

被引：26

作者：

Berree, F ^{[1
]}

Chang, KY ^{[1
]}

Cobas, A ^{[1
]}

Rapoport, H ^{[1
]}

机构：

[1] UNIV CALIF BERKELEY,DEPT CHEM,BERKELEY,CA 94720

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 02期

关键词：

D O I：

10.1021/jo951754c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A process has been developed for transforming the beta-carboxyl of aspartate and the gamma-carboxyl of glutamate into anisolyl ketones. These ketones are occasional byproducts in peptide synthesis, resulting from deprotection or resin-removal processes in the presence of anisole as a scavenger. The ketone amino acids have been incorporated in a tripeptide by coupling with CBMIT. During peptide bond formation-the keto group of the glutamyl residue required protection, which was provided as the ethylene dithioketal.

引用

收藏

页码：715 / 721

页数：7

相关论文

共 26 条

[1] HIGHLY STEREOSELECTIVE TOTAL SYNTHESES OF (+)-ALLOPUMILIOTOXIN-267A AND (+)-ALLOPUMILIOTOXIN-339A VIA INTRAMOLECULAR NICKEL(II) CHROMIUM(II)-MEDIATED CYCLIZATION [J].

AOYAGI, S ;

WANG, TC ;

KIBAYASHI, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11393-11409

[2]

BALDWIN JE, 1993, SYNLETT, P51

[3] CHIROSPECIFIC SYNTHESIS OF (1S,3R)-1-AMINO-3-(HYDROXYMETHYL)CYCLOPENTANE, PRECURSOR FOR CARBOCYCLIC NUCLEOSIDE SYNTHESIS - DIECKMANN CYCLIZATION WITH AN ALPHA-AMINO-ACID [J].

BERGMEIER, SC ;

COBAS, AA ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (09) :2369-2376

[4]

BURGER K, 1991, LIEBIGS ANN CHEM, P1365

[5] ALPHA-AMINO-ACIDS AS CHIRAL EDUCTS FOR ASYMMETRIC PRODUCTS - THE SYNTHESIS OF ALPHA'-AMINO-ALPHA, BETA-YNONES [J].

CUPPS, TL ;

BOUTIN, RH ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (21) :3972-3979

[6] PHOTOSENSITIZED CLEAVAGE OF THE DITHIOPROTECTING GROUP BY VISIBLE-LIGHT [J].

EPLING, GA ;

WANG, QX .

TETRAHEDRON LETTERS, 1992, 33 (40) :5909-5912

[7]

EPLING GA, 1992, SYNLETT, V335

[8] REGIOSELECTIVE NUCLEOPHILIC-ATTACK ON N-BOC-PYROGLUTAMATE ETHYL-ESTER [J].

EZQUERRA, J ;

DEMENDOZA, J ;

PEDREGAL, C ;

RAMIREZ, C .

TETRAHEDRON LETTERS, 1992, 33 (38) :5589-5590

[9] NUCLEAR MAGNETIC RESONANCE AND ULTRAVIOLET SPECTROSCOPY OF SUBSTITUTED AROMATIC ORGANOMETALLIC COMPOUNDS OF LITHIUM MAGNESIUM AND CALCIUM [J].

FRAENKEL, G ;

DAYAGI, S ;

KOBAYASH.S .

JOURNAL OF PHYSICAL CHEMISTRY, 1968, 72 (03) :953-&

[10] SELECTIVE REMOVAL OF AN N-BOC PROTECTING GROUP IN THE PRESENCE OF A TERT-BUTYL ESTER AND OTHER ACID-SENSITIVE GROUPS [J].

GIBSON, FS ;

BERGMEIER, SC ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3216-3218